Stereospezifische asymmetrische Synthese tertiärer Allylalkohol‐ Derivate über katalytische (2,3)‐Meisenheimer‐Umlagerungen
Abstract: Chirale azyklische tertiäre Allylalkohole sind bedeutende Synthesebausteine, deren enantioselektive Synthese eine anspruchsvolle Aufgabe ist. Eine wesentliche Einschränkung bei katalytisch asymmetrischen 1,2‐Additionen an Ketone ist die Enantioseitendifferenzierung durch sterische Unterscheidung beider Ketonreste. Um dieses Problem zu überwinden, entwickelten wir eine katalytisch asymmetrische Meisenheimer‐Umlagerung, die auf stereospezifische Weise abläuft. Dabei können selbst Produkte, bei denen die Reste am generierten quartären Stereozentrum einen ähnlichen sterischen Anspruch aufweisen, mit hoher Enantioselektivität hergestellt werden. Niedrige Katalysatorbeladungen genügen, und die Bedingungen sind mild genug, um reaktive funktionelle Gruppen wie enolisierbare Aldehyde, primäre Tosylate oder Epoxide zu tolerieren. Unsere Untersuchungen lassen auf eine intramolekulare Umlagerung schließen.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Stereospezifische asymmetrische Synthese tertiärer Allylalkohol‐ Derivate über katalytische (2,3)‐Meisenheimer‐Umlagerungen ; volume:132 ; number:27 ; year:2020 ; pages:11037-11041 ; extent:5
Angewandte Chemie ; 132, Heft 27 (2020), 11037-11041 (gesamt 5)
- Creator
- DOI
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10.1002/ange.202001725
- URN
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urn:nbn:de:101:1-2022052911243816528576
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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2025-08-15T07:35:14+0200
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Associated
- Yu, Xin
- Wannenmacher, Nick
- Peters, René
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